JP3663528B2 - Pyridophenoxazine metal chelate compound - Google Patents
Pyridophenoxazine metal chelate compound Download PDFInfo
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- JP3663528B2 JP3663528B2 JP35730496A JP35730496A JP3663528B2 JP 3663528 B2 JP3663528 B2 JP 3663528B2 JP 35730496 A JP35730496 A JP 35730496A JP 35730496 A JP35730496 A JP 35730496A JP 3663528 B2 JP3663528 B2 JP 3663528B2
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- C—CHEMISTRY; METALLURGY
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Description
【０００１】
【発明の属する技術分野】
本発明は、新規な金属キレート化合物に関し、詳しくは有機溶媒に対する溶解性が高く、塗布によるコーティングが可能で、しかも耐光性に優れた、光記録媒用記録材料として有用なピリドフェノオキサジン金属キレート化合物に関する。
【０００２】
【従来の技術】
従来、有機色素薄膜を記録層とする記録媒体において、該有機色素薄膜にフタロシアニン化合物を使用したもの（例えば特開昭５８−１８３２９６号公報その他）、シアニン系色素を使用したもの（例えば特開昭５７−８２０９３号公報その他）、あるいはフェナレン系色素、ナフトキノン系色素などを使用したものが知られている。たゞ、フタロシアニン化合物は、熱、光等に対する安定性が極めて高いため、情報記録感度が低く記録に時間を要するし、また有機溶剤への溶解性が乏しく、従来は蒸着法しか薄膜化はできず生産性が悪いという難点を有している。フェナレン系色素又はナフトキノン系色素は、蒸着させやすい利点を有する反面、反射率が低いという欠点がある。シアニン系色素は、塗布によるコーティングが容易であるという利点を有する反面、耐光性に劣り、再生光による劣化を起こすという欠点がある。
【０００３】
加えて、近年、従来の光ディスクで使用されてきた波長域より短波長に発振波長（６３０〜７２０ｎｍ）を有する半導体レーザーが実用化されはじめている。更に、基板上に有機色素、金属反射層、保護層を順次積層してなるＣＤ−Ｒ媒体は、そのＣＤ規格を満足するには高い反射率を必要とし、そのため再生波長域（７７０〜８３０ｎｍ）に高い屈折率を有し、且つ安定性の高い有機色素の開発が必要である。
【０００４】
【発明が解決しようとする課題】
従って、本発明は有機溶媒に対する溶解性が高く、塗布によるコーティングが可能で、しかも耐光性に優れた、光記録媒用記録材料として有用な、新規な化合物を提供することを目的とする。
【０００５】
【課題を解決するための手段】
本発明によれば、第一に、下記一般式（Ｉ）で示されるピリドフェノオキサジン金属キレート化合物が提供される。
【化１】
Ｍ：Ｆｅ、Ｃｏ、Ｎｉ、Ｃｕ又はＺｎ金属原子、
Ｒ1、Ｒ2：それぞれ独立に、置換若しくは無置換のアルキル基、又は置換若しくは無置換のアリール基、
Ｘ：陰イオン、
ｎ：２又は３。）
第二に、前記一般式（Ｉ）において、Ｒ1及びＲ2がそれぞれ独立に、置換若しくは無置換のアルキル基である上記第一に記載したピリドフェノオキサジン金属キレート化合物が提供される。
【０００６】
本発明の前記一般式（Ｉ）で示される新規な金属キレート化合物は、有機溶剤に対する溶解性が高く、生産性の高い溶剤塗工が可能であり、耐光性及び安定性に優れた、しかも分解点が２５０℃以下と低い色素である。従って、該色素は光記録媒体用の記録材料として特に有用であり、該色素を含有することにより、生産性安定性の高い、高耐光、高感度、高速記録が可能な光記録媒体が提供される。
【０００７】
【発明の実施の形態】
以下、本発明を詳しく説明する。
本発明は、上記したように下記一般式（Ｉ）で示されるピリドフェノオキサジン金属キレート化合物に関するものであるが、このピリドフェノオキサジン金属キレート化合物は、新規物質である。
【化１】
前記一般式（Ｉ）で示されるピリドフェノオキサジン金属キレート化合物において、ＭはＦｅ、Ｃｏ、Ｎｉ、Ｃｕ又はＺｎ金属原子を表す。
【０００９】
前記一般式（Ｉ）において、Ｒ1及びＲ2は、それぞれ独立に、置換若しくは無置換のアルキル基、又は置換若しくは無置換のアリール基を表すが、Ｒ1及びＲ2のアルキル基の具体例としては、次のものが挙げられる。
メチル基、エチル基、ｎ−プロピル基、ｎ−ブチル基、ｎ−ペンチル基、ｎ−ヘキシル基、ｎ−ヘプチル基、ｎ−オクチル基、ｎ−ノニル基、ｎ−デシル基等の一級アルキル基；イソプロピル基、イソブチル基、ｓｅｃ−ブチル基、イソアミル基等の二級アルキル基；ネオペンチル基、ｔｅｒｔ−ブチル基、ｔｅｒｔ−ヘキシル基、ｔｅｒｔ−アミル基、ｔｅｒｔ−オクチル基等の三級アルキル基；シクロヘキシル基等のシクロアルキル基等。
【００１０】
また、アリール基としては、フェニル基、エチルフェニル基、ブチルフェニル基、ナフチル基等が挙げられる。アリール基としては、フェニルチオエチル基、メチルチオエチル基、ブチルチオエチル基等が、窒素を介して置換されているアリール基としては、ジメチルアミノフェニル基、ジブチルアミノフェニル基等が挙げられる。
【００１１】
また、前記一般式（Ｉ）において、Ｘは陰イオンを表すが、その具体例としては、表１に示すようなものが挙げられる。
【表１】
本発明のピリドフェノオキサジン金属キレート化合物は、例えば次の方法によって製造することができる。
まず、例えば日本化学会第６８秋季年会講演予稿集５０２頁に記載の方法に従って配位子を得る。すなわち、下記一般式（ＩＩ）で示される化合物と、下記一般式（ＩＩＩ）で示される化合物とを反応させ下記一般式（ＩＶ）で示される配粒子を得る。
【化２】
【化４】
次いで、上記一般式（ＩＶ）で示される配位子と下記一般式（Ｖ）で示される金属塩とを反応させることにより、前記一般式（Ｉ）で示される化合物を得ることができる。
ＭＸ ・・・・・（Ｖ）
（式中、Ｍ及びＸは前記定義に同じ。）
【００１３】
本発明の前記一般式（Ｉ）で示される金属キレート化合物の具体例としては、例えば表２−（１）及び表２−（２）で示されるものが挙げられる。
【００１４】
【表２−（１）】
【表２−（２）】
本発明の前記一般式（Ｉ）で示されるピリドフェノオキサジン金属キレート化合物は、有機溶媒に対する溶解性が高く、塗布によるコーティングが可能で、しかも耐光性に優れた新規な金属キレート化合物であり、光情報記録用材料として極めて有用な化合物である。
【００１７】
【実施例】
以下、実施例により本発明を具体的に説明する。
実施例１
下記構造式（Ａ）で示される化合物１０．０ｇ及び下記構造式（Ｂ）で示される化合物９．５ｇを、Ｃｕ（ＯＣＯＣＨ3）2１０．５ｇを含む酢酸５０ｍｌに加え、５時間撹拌した。反応液に氷水を加え、沈殿物を濾取した。沈殿物はクロロホルムにより抽出し、クロロホルム層を濃縮、カラムクロマトグラム法により下記構造式（Ｃ）で示される目的配位子１１．９ｇ収率６５％を分離精製した。次に、構造式（Ｃ）で示される配位子２．０ｇをテトラヒドロフラン１００ｍｌに溶解させた後、室温にてＮｉ（ＣｌＯ4）2６Ｈ2Ｏ ２．３ｇを加え、濾過した後、濾液を放置し、析出した結晶を濾取し、下記構造式（Ｄ）で示される金属キレート化合物１．７ｇを得た。
得られた金属キレート化合物の可視部の吸収スペクトルは、λｍａｘ６１０ｎｍ（トルエン中）、分解開始温度２４０℃であった。
【００１８】
【化５】
実施例２
前記構造式（Ａ）で示される化合物５．２ｇ及び下記構造式（Ｅ）で示される化合物１０．０ｇを、ＦｅＣｌ3 ４．９ｇを含む酢酸３０ｍｌに加え、１０時間撹拌した。反応液に氷水を加え、沈殿物を濾取した。沈殿物はクロロホルムにより抽出し、クロロホルム層を濃縮、カラムクロマトグラム法により下記構造式（Ｆ）で示される目的配位子８．５ｇ収率５８％を分離精製した。次に、構造式（Ｆ）で示される配位子１．０ｇをエタノール３０ｍｌに溶解させた後、室温にてＣｕＳＯ4５Ｈ2Ｏ ０．５ｇを加え、濾過した後、濾液に水を加え、析出した結晶を濾取、水洗し、下記構造式（Ｇ）で示される金属キレート化合物１．２ｇを得た。
得られた金属キレート化合物の可視部の吸収スペクトルは、λｍａｘ６１４ｎｍ（トルエン中）、分解開始温度２２０℃であった。得られた金属キレート化合物のクロロホルム溶液中の可視吸収スペクトルを図１に、また該化合物の吸収スペクトルを図３に示す。
【００２０】
【化９】
実施例３
前記構造式（Ｆ）で示される配位子１．０ｇをエタノール３０ｍｌに溶解させた後、室温にてＣｏＳＯ4７Ｈ2Ｏ ０．６ｇを加え、濾過した後、濾液に水を加え、析出した結晶を濾取、水洗し、下記構造式（Ｈ）で示される金属キレート化合物１．１ｇを得た。
得られた金属キレート化合物の可視部の吸収スペクトルは、λｍａｘ６４８ｎｍ（アセトニトリル中）であった。得られた金属キレート化合物のメタノール溶液中の可視吸収スペクトルを図２に示す。
【００２２】
【化１２】
【発明の効果】
本発明のピリドフェノオキサジン金属キレート化合物は前記一般式（Ｉ）で示される構造を有することから、有機溶媒に対する溶解性が高く、生産性の高い溶剤塗工によるコーティング可能であり、しかも耐光性に優れ、その上分解点が２５０℃以下と低い色素である。従って、特に光記録媒用の記録材料として極めて有用である。
【図面の簡単な説明】
【図１】本発明の実施例２で得られた銅キレート化合物のクロロホルム溶液中の可視吸収スペクトルを表す図である。
【図２】本発明の実施例３で得られたコバルトキレート化合物のメタノール溶液中の可視吸収スペクトルを表す図である。
【図３】本発明の実施例２で得られた銅キレート化合物の赤外吸収スペクトルを表す図である。[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel metal chelate compound, and more specifically, pyridophenoxazine metal chelate useful as a recording material for optical recording media, which has high solubility in organic solvents, can be coated by coating, and has excellent light resistance. Relates to compounds.
[0002]
[Prior art]
Conventional recording media having an organic dye thin film as a recording layer, wherein the organic dye thin film uses a phthalocyanine compound (for example, JP-A No. 58-183296 and others), and uses a cyanine dye (for example, JP-A No. Sho). No. 57-82093 and others), or those using phenalene dyes, naphthoquinone dyes, and the like are known. On the other hand, phthalocyanine compounds have extremely high stability to heat, light, etc., so the information recording sensitivity is low and recording takes time, and the solubility in organic solvents is poor. It has the disadvantage that productivity is poor. Phenalene dyes or naphthoquinone dyes have the advantage of being easy to deposit, but have the disadvantage of low reflectivity. While the cyanine dye has an advantage that coating by application is easy, it has a disadvantage that it is inferior in light resistance and causes deterioration due to reproduction light.
[0003]
In addition, in recent years, semiconductor lasers having an oscillation wavelength (630 to 720 nm) shorter than the wavelength range used in conventional optical disks have been put into practical use. Furthermore, a CD-R medium in which an organic dye, a metal reflective layer, and a protective layer are sequentially laminated on a substrate requires a high reflectivity to satisfy the CD standard, and therefore a reproduction wavelength region (770 to 830 nm). Therefore, it is necessary to develop an organic dye having a high refractive index and high stability.
[0004]
[Problems to be solved by the invention]
Accordingly, an object of the present invention is to provide a novel compound useful as a recording material for an optical recording medium, which has high solubility in an organic solvent, can be coated by coating, and has excellent light resistance.
[0005]
[Means for Solving the Problems]
According to the present invention, first, a pyridophenoxazine metal chelate compound represented by the following general formula (I) is provided.
[Chemical 1]
M: Fe, Co, Ni, Cu or Zn metal atom,
R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
X: anion,
n: 2 or 3. )
Second, there is provided the pyridophenoxazine metal chelate compound described in the above first, wherein, in the general formula (I), R 1 and R 2 are each independently a substituted or unsubstituted alkyl group.
[0006]
The novel metal chelate compound represented by the general formula (I) of the present invention has high solubility in organic solvents, enables high-productivity solvent coating, has excellent light resistance and stability, and is decomposed. It is a dye having a low point of 250 ° C. or lower. Therefore, the dye is particularly useful as a recording material for an optical recording medium. By containing the dye, an optical recording medium capable of high productivity stability, high light resistance, high sensitivity, and high-speed recording is provided. The
[0007]
DETAILED DESCRIPTION OF THE INVENTION
The present invention will be described in detail below.
The present invention relates to a pyridophenoxazine metal chelate compound represented by the following general formula (I) as described above, and this pyridophenoxazine metal chelate compound is a novel substance.
[Chemical 1]
In the pyridophenoxazine metal chelate compound represented by the general formula (I), M represents an Fe, Co, Ni, Cu or Zn metal atom.
[0009]
In the general formula (I), R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. Specific examples of the alkyl group represented by R 1 and R 2 Examples include the following.
Primary alkyl group such as methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group and n-decyl group Secondary alkyl groups such as isopropyl group, isobutyl group, sec-butyl group and isoamyl group; tertiary alkyl groups such as neopentyl group, tert-butyl group, tert-hexyl group, tert-amyl group and tert-octyl group; A cycloalkyl group such as a cyclohexyl group;
[0010]
In addition, examples of the aryl group include a phenyl group, an ethylphenyl group, a butylphenyl group, and a naphthyl group. Examples of the aryl group include a phenylthioethyl group, a methylthioethyl group, a butylthioethyl group and the like, and examples of the aryl group substituted with nitrogen include a dimethylaminophenyl group and a dibutylaminophenyl group.
[0011]
Moreover, in the said general formula (I), X represents an anion, As a specific example, what is shown in Table 1 is mentioned.
[Table 1]
The pyridophenoxazine metal chelate compound of the present invention can be produced, for example, by the following method.
First, a ligand is obtained according to the method described in, for example, the 68th Autumn Meeting of the Chemical Society of Japan, page 502. That is, a compound represented by the following general formula (II) and a compound represented by the following general formula (III) are reacted to obtain particles having the following general formula (IV).
[Chemical formula 2]
[Formula 4]
Subsequently, the compound shown by the said general formula (I) can be obtained by making the ligand shown by the said general formula (IV), and the metal salt shown by the following general formula (V) react.
MX (V)
(In the formula, M and X are the same as defined above.)
[0013]
Specific examples of the metal chelate compound represented by the general formula (I) of the present invention include those shown in Table 2- (1) and Table 2- (2).
[0014]
[Table 2- (1)]
[Table 2- (2)]
The pyridophenoxazine metal chelate compound represented by the general formula (I) of the present invention is a novel metal chelate compound having high solubility in an organic solvent, coating by coating, and excellent light resistance. It is a very useful compound as an optical information recording material.
[0017]
【Example】
Hereinafter, the present invention will be described specifically by way of examples.
Example 1
10.0 g of a compound represented by the following structural formula (A) and 9.5 g of a compound represented by the following structural formula (B) were added to 50 ml of acetic acid containing 10.5 g of Cu (OCOCH 3 ) 2 and stirred for 5 hours. Ice water was added to the reaction solution, and the precipitate was collected by filtration. The precipitate was extracted with chloroform, the chloroform layer was concentrated, and a 11.9 g yield 65% yield of the target ligand represented by the following structural formula (C) was separated and purified by a column chromatogram method. Next, 2.0 g of the ligand represented by the structural formula (C) was dissolved in 100 ml of tetrahydrofuran, 2.3 g of Ni (ClO 4 ) 2 6H 2 O was added at room temperature, and the filtrate was filtered. Then, the precipitated crystals were collected by filtration to obtain 1.7 g of a metal chelate compound represented by the following structural formula (D).
The absorption spectrum of the visible part of the obtained metal chelate compound was λmax 610 nm (in toluene), and the decomposition start temperature was 240 ° C.
[0018]
[Chemical formula 5]
Example 2
The FeCl 3 was mixed with 5.2 g of the compound represented by the structural formula (A) and 10.0 g of the compound represented by the following structural formula (E). The mixture was added to 30 ml of acetic acid containing 4.9 g and stirred for 10 hours. Ice water was added to the reaction solution, and the precipitate was collected by filtration. The precipitate was extracted with chloroform, the chloroform layer was concentrated, and the target ligand 8.5 g represented by the following structural formula (F) was separated and purified by a column chromatogram method. Next, 1.0 g of the ligand represented by the structural formula (F) was dissolved in 30 ml of ethanol, 0.5 g of CuSO 4 5H 2 O was added at room temperature and filtered, and then water was added to the filtrate. The precipitated crystals were collected by filtration and washed with water to obtain 1.2 g of a metal chelate compound represented by the following structural formula (G).
The absorption spectrum of the visible part of the obtained metal chelate compound was λmax 614 nm (in toluene) and the decomposition start temperature was 220 ° C. A visible absorption spectrum of the obtained metal chelate compound in a chloroform solution is shown in FIG. 1, and an absorption spectrum of the compound is shown in FIG.
[0020]
[Chemical 9]
Example 3
After dissolving 1.0 g of the ligand represented by the structural formula (F) in 30 ml of ethanol, adding 0.6 g of CoSO 4 7H 2 O at room temperature and filtering, water was added to the filtrate to precipitate. The crystals were collected by filtration and washed with water to obtain 1.1 g of a metal chelate compound represented by the following structural formula (H).
The absorption spectrum of the visible part of the obtained metal chelate compound was λmax 648 nm (in acetonitrile). The visible absorption spectrum in the methanol solution of the obtained metal chelate compound is shown in FIG.
[0022]
Embedded image
【The invention's effect】
Since the pyridophenoxazine metal chelate compound of the present invention has the structure represented by the general formula (I), it is highly soluble in an organic solvent, can be coated by a highly productive solvent coating, and has light resistance. In addition, the pigment has a decomposition point as low as 250 ° C. or lower. Therefore, it is extremely useful as a recording material for an optical recording medium.
[Brief description of the drawings]
FIG. 1 is a diagram showing a visible absorption spectrum of a copper chelate compound obtained in Example 2 of the present invention in a chloroform solution.
FIG. 2 is a view showing a visible absorption spectrum in a methanol solution of the cobalt chelate compound obtained in Example 3 of the present invention.
FIG. 3 is an infrared absorption spectrum of the copper chelate compound obtained in Example 2 of the present invention.
Claims (2)
Ｍ：Ｆｅ、Ｃｏ、Ｎｉ、Ｃｕ又はＺｎ金属原子、
Ｒ1、Ｒ2：それぞれ独立に、置換若しくは無置換のアルキル基、又は置換若しくは無置換のアリール基、
Ｘ：陰イオン、
ｎ：２又は３。）The pyridophenoxazine metal chelate compound shown by the following general formula (I).
M: Fe, Co, Ni, Cu or Zn metal atom,
R 1 and R 2 each independently represents a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group,
X: anion,
n: 2 or 3. )
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35730496A JP3663528B2 (en) | 1996-12-26 | 1996-12-26 | Pyridophenoxazine metal chelate compound |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35730496A JP3663528B2 (en) | 1996-12-26 | 1996-12-26 | Pyridophenoxazine metal chelate compound |
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| Publication Number | Publication Date |
|---|---|
| JPH10182651A JPH10182651A (en) | 1998-07-07 |
| JP3663528B2 true JP3663528B2 (en) | 2005-06-22 |
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| JP35730496A Expired - Fee Related JP3663528B2 (en) | 1996-12-26 | 1996-12-26 | Pyridophenoxazine metal chelate compound |
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| Country | Link |
|---|---|
| JP (1) | JP3663528B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH11208118A (en) * | 1997-11-20 | 1999-08-03 | Taiyo Yuden Co Ltd | Optical information recording medium |
| JP2007119481A (en) * | 1999-01-27 | 2007-05-17 | Mitsubishi Chemicals Corp | Compound for forming organic layer of organic electric field light-emitting element, and organic electric field light-emitting element by using the same |
| CN114773361B (en) * | 2022-04-15 | 2023-04-11 | 山东第一医科大学(山东省医学科学院) | N-heteronile erythronium salt compound and preparation method and application thereof |
-
1996
- 1996-12-26 JP JP35730496A patent/JP3663528B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10182651A (en) | 1998-07-07 |
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